KR20210106998A - 용이하게 처리가능하고 열적으로 안정한 인 함유 난연성 물질을 제조하는 방법 - Google Patents
용이하게 처리가능하고 열적으로 안정한 인 함유 난연성 물질을 제조하는 방법 Download PDFInfo
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- KR20210106998A KR20210106998A KR1020217018527A KR20217018527A KR20210106998A KR 20210106998 A KR20210106998 A KR 20210106998A KR 1020217018527 A KR1020217018527 A KR 1020217018527A KR 20217018527 A KR20217018527 A KR 20217018527A KR 20210106998 A KR20210106998 A KR 20210106998A
- Authority
- KR
- South Korea
- Prior art keywords
- flame retardant
- metal
- polyamide
- oxide
- alkyl
- Prior art date
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 171
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 138
- 239000000463 material Substances 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 61
- 230000008569 process Effects 0.000 title claims abstract description 17
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 title 1
- 239000002904 solvent Substances 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 42
- 239000002245 particle Substances 0.000 claims abstract description 41
- 238000009835 boiling Methods 0.000 claims abstract description 40
- 239000000843 powder Substances 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims description 115
- 229920000642 polymer Polymers 0.000 claims description 81
- 229910052751 metal Inorganic materials 0.000 claims description 59
- 239000002184 metal Substances 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- -1 poly-alkylene terephthalate Chemical compound 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000004952 Polyamide Substances 0.000 claims description 38
- 229920002647 polyamide Polymers 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000002002 slurry Substances 0.000 claims description 25
- 229910052782 aluminium Inorganic materials 0.000 claims description 23
- 239000000725 suspension Substances 0.000 claims description 23
- 229920000877 Melamine resin Polymers 0.000 claims description 21
- 239000011575 calcium Substances 0.000 claims description 21
- IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 claims description 21
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000011701 zinc Substances 0.000 claims description 19
- 229910052791 calcium Inorganic materials 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229910052725 zinc Inorganic materials 0.000 claims description 17
- 150000001768 cations Chemical class 0.000 claims description 16
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 229910052742 iron Inorganic materials 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 claims description 12
- 239000002671 adjuvant Substances 0.000 claims description 11
- 239000011521 glass Substances 0.000 claims description 11
- 229910044991 metal oxide Inorganic materials 0.000 claims description 11
- 150000004706 metal oxides Chemical class 0.000 claims description 11
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 10
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 229920001955 polyphenylene ether Polymers 0.000 claims description 10
- 150000003457 sulfones Chemical class 0.000 claims description 10
- 229920002292 Nylon 6 Polymers 0.000 claims description 9
- 229910052787 antimony Inorganic materials 0.000 claims description 9
- 229910001463 metal phosphate Inorganic materials 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 8
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 8
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 239000003822 epoxy resin Substances 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 150000007974 melamines Chemical class 0.000 claims description 8
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 8
- 235000021317 phosphate Nutrition 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 229920000647 polyepoxide Polymers 0.000 claims description 8
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 7
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 7
- 239000007859 condensation product Substances 0.000 claims description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 7
- 229920000515 polycarbonate Polymers 0.000 claims description 7
- 239000004417 polycarbonate Substances 0.000 claims description 7
- 229920002635 polyurethane Polymers 0.000 claims description 7
- 239000004814 polyurethane Substances 0.000 claims description 7
- 229910052718 tin Inorganic materials 0.000 claims description 7
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 6
- 150000004692 metal hydroxides Chemical class 0.000 claims description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000454 talc Substances 0.000 claims description 6
- 229910052623 talc Inorganic materials 0.000 claims description 6
- 229910052726 zirconium Inorganic materials 0.000 claims description 6
- 241000219112 Cucumis Species 0.000 claims description 5
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 5
- 239000006229 carbon black Substances 0.000 claims description 5
- 239000004927 clay Substances 0.000 claims description 5
- 229910052570 clay Inorganic materials 0.000 claims description 5
- 239000010439 graphite Substances 0.000 claims description 5
- 229910002804 graphite Inorganic materials 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000004954 Polyphthalamide Substances 0.000 claims description 4
- 239000005083 Zinc sulfide Substances 0.000 claims description 4
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 claims description 4
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 claims description 4
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 4
- 229910052788 barium Inorganic materials 0.000 claims description 4
- IUTYMBRQELGIRS-UHFFFAOYSA-N boric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OB(O)O.NC1=NC(N)=NC(N)=N1 IUTYMBRQELGIRS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- YZYDPPZYDIRSJT-UHFFFAOYSA-K boron phosphate Chemical compound [B+3].[O-]P([O-])([O-])=O YZYDPPZYDIRSJT-UHFFFAOYSA-K 0.000 claims description 4
- 229910000149 boron phosphate Inorganic materials 0.000 claims description 4
- 239000000378 calcium silicate Substances 0.000 claims description 4
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 4
- BIOOACNPATUQFW-UHFFFAOYSA-N calcium;dioxido(dioxo)molybdenum Chemical compound [Ca+2].[O-][Mo]([O-])(=O)=O BIOOACNPATUQFW-UHFFFAOYSA-N 0.000 claims description 4
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002041 carbon nanotube Substances 0.000 claims description 4
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 4
- TWSNDAGGXNPFMX-UHFFFAOYSA-N dialuminum hydrogen phosphite Chemical compound [Al+3].[Al+3].OP([O-])[O-].OP([O-])[O-].OP([O-])[O-] TWSNDAGGXNPFMX-UHFFFAOYSA-N 0.000 claims description 4
- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 claims description 4
- 229920005669 high impact polystyrene Polymers 0.000 claims description 4
- 239000004797 high-impact polystyrene Substances 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 4
- 229960001545 hydrotalcite Drugs 0.000 claims description 4
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 4
- 239000001095 magnesium carbonate Substances 0.000 claims description 4
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- 239000000347 magnesium hydroxide Substances 0.000 claims description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 4
- 239000000395 magnesium oxide Substances 0.000 claims description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 4
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 4
- 229920006375 polyphtalamide Polymers 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 claims description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 4
- 229910001887 tin oxide Inorganic materials 0.000 claims description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 4
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000010455 vermiculite Substances 0.000 claims description 4
- 229910052902 vermiculite Inorganic materials 0.000 claims description 4
- 235000019354 vermiculite Nutrition 0.000 claims description 4
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 4
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 4
- 229910052984 zinc sulfide Inorganic materials 0.000 claims description 4
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 claims description 4
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 claims description 4
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims description 4
- BHTBHKFULNTCHQ-UHFFFAOYSA-H zinc;tin(4+);hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Sn+4] BHTBHKFULNTCHQ-UHFFFAOYSA-H 0.000 claims description 4
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 4
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- 229920001890 Novodur Polymers 0.000 claims description 3
- 229920000299 Nylon 12 Polymers 0.000 claims description 3
- YHZHRJXUKMQJOA-UHFFFAOYSA-N O=P(Cc1ccc(cc1)-c1ccc(CP(=O)(c2ccccc2)c2ccccc2)cc1)(c1ccccc1)c1ccccc1 Chemical group O=P(Cc1ccc(cc1)-c1ccc(CP(=O)(c2ccccc2)c2ccccc2)cc1)(c1ccccc1)c1ccccc1 YHZHRJXUKMQJOA-UHFFFAOYSA-N 0.000 claims description 3
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims description 3
- XSAOTYCWGCRGCP-UHFFFAOYSA-K aluminum;diethylphosphinate Chemical compound [Al+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC XSAOTYCWGCRGCP-UHFFFAOYSA-K 0.000 claims description 3
- QVKQNISQFCPYGN-UHFFFAOYSA-K aluminum;dimethylphosphinate Chemical compound [Al+3].CP(C)([O-])=O.CP(C)([O-])=O.CP(C)([O-])=O QVKQNISQFCPYGN-UHFFFAOYSA-K 0.000 claims description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- YHQWVGMMYOGEAW-UHFFFAOYSA-N methylidene(diphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=C)C1=CC=CC=C1 YHQWVGMMYOGEAW-UHFFFAOYSA-N 0.000 claims description 3
- 229920000090 poly(aryl ether) Polymers 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 3
- OMSYGYSPFZQFFP-UHFFFAOYSA-J zinc pyrophosphate Chemical compound [Zn+2].[Zn+2].[O-]P([O-])(=O)OP([O-])([O-])=O OMSYGYSPFZQFFP-UHFFFAOYSA-J 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- 229920003189 Nylon 4,6 Polymers 0.000 claims description 2
- 229920006153 PA4T Polymers 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- IOGRQIWFIRKXQV-UHFFFAOYSA-K aluminum dipropylphosphinate Chemical compound C(CC)P([O-])(=O)CCC.[Al+3].C(CC)P([O-])(=O)CCC.C(CC)P([O-])(=O)CCC IOGRQIWFIRKXQV-UHFFFAOYSA-K 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229920001971 elastomer Polymers 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052914 metal silicate Inorganic materials 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- YSUVXWLFCHRCMI-UHFFFAOYSA-N phosphorosomethylbenzene Chemical compound O=PCC1=CC=CC=C1 YSUVXWLFCHRCMI-UHFFFAOYSA-N 0.000 claims description 2
- 229920006128 poly(nonamethylene terephthalamide) Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000005060 rubber Substances 0.000 claims description 2
- SLKRGHBFYYVSLH-UHFFFAOYSA-K tris(dibutylphosphoryloxy)alumane Chemical compound [Al+3].CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC SLKRGHBFYYVSLH-UHFFFAOYSA-K 0.000 claims description 2
- 229920000307 polymer substrate Polymers 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 229930182556 Polyacetal Natural products 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
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| PCT/US2019/067221 WO2020132095A1 (en) | 2018-12-20 | 2019-12-18 | Method for preparing readily processable, thermally-stable, phosphorus-containing flame retardant material |
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| CN116814136B (zh) * | 2023-06-20 | 2024-04-19 | 西南石油大学 | 一种pap活性碳球基水性环氧膨胀防火涂料的制备方法 |
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| DE1668883A1 (de) | 1968-01-25 | 1971-02-11 | Dynamit Nobel Ag | Verfahren zur Herstellung von halogenierten Estern der Phosphorsaeuren |
| DE2252210A1 (de) | 1972-10-25 | 1974-05-09 | Hoechst Ag | Schwerentflammbare thermoplastische polyester |
| GB8611357D0 (en) | 1986-05-09 | 1986-06-18 | Ciba Geigy Ag | Flame retardent polymer compositions |
| US4859466A (en) * | 1986-12-23 | 1989-08-22 | Ciba-Geigy Corporation | Microbicides |
| DE3833977A1 (de) | 1988-10-06 | 1990-04-26 | Bayer Ag | Addukte aus phosphonaten und aminen und deren verwendung zum vorbeugenden brandschutz |
| DE3912552A1 (de) | 1989-04-17 | 1990-10-18 | Bayer Ag | Waermebestaendige schaumstoffe, deren herstellung und verwendung |
| US5420326A (en) * | 1994-05-12 | 1995-05-30 | Akzo Nobel N.V. | Bis(pentaerythritol phosphate alcohol) hydrogen phosphonate |
| DE4430932A1 (de) | 1994-08-31 | 1996-03-07 | Hoechst Ag | Flammgeschützte Polyesterformmasse |
| DE19614424A1 (de) | 1996-04-12 | 1997-10-16 | Hoechst Ag | Synergistische Flammschutzmittel-Kombination für Polymere |
| ATE313597T1 (de) | 1999-01-30 | 2006-01-15 | Clariant Gmbh | Flammschutzmittel-kombination für thermoplastische polymere i |
| DE19933901A1 (de) | 1999-07-22 | 2001-02-01 | Clariant Gmbh | Flammschutzmittel-Kombination |
| DE10014593C2 (de) | 2000-03-27 | 2002-06-27 | Clariant Gmbh | Halogenfreier, flammwidriger Polyurethanhartschaum und ein Verfahren zu seiner Herstellung |
| WO2004046235A1 (en) | 2002-11-21 | 2004-06-03 | Ciba Specialty Chemicals Holding Inc. | Flame retardant composition comprising a phosphonic acid metal salt and a nitrogen-containing compound |
| JP2006001876A (ja) * | 2004-06-17 | 2006-01-05 | Songwon Industrial Co Ltd | 機能性有機りん化合物およびその製造方法 |
| DE102005036653A1 (de) | 2005-08-04 | 2007-02-08 | Lanxess Deutschland Gmbh | Flammschutzmittelzubereitung |
| US20090275682A1 (en) * | 2005-11-10 | 2009-11-05 | Asahi Kasei Chemicals Corporation | Resin Composition Excellent in Flame Retardance |
| JP5992906B2 (ja) * | 2010-06-24 | 2016-09-14 | アイシーエル−アイピー アメリカ インコーポレイテッド | 金属ホスホネート難燃剤およびその製造方法 |
| DE102010048025A1 (de) | 2010-10-09 | 2012-04-12 | Clariant International Ltd. | Flammschutzmittel- Stabilisator-Kombination für thermoplastische Polymere |
| US8747709B2 (en) * | 2012-05-03 | 2014-06-10 | Empire Technology Development Llc | Phosphonate-substituted lignin as a flame retardant |
| US9752011B2 (en) | 2013-07-24 | 2017-09-05 | Lanxess Solutions Us Inc. | Phosphorus containing flame retardants |
| US9765204B2 (en) | 2013-07-24 | 2017-09-19 | Lanxess Solutions Us Inc. | Halogen free high temperature polyamide compositions comprising phosphorus containing flame retardants |
| US9745449B2 (en) | 2013-07-24 | 2017-08-29 | Lanxess Solutions Us Inc. | Phosphorus containing flame retardants |
| PL3172217T3 (pl) * | 2014-07-22 | 2022-01-17 | Lanxess Corporation | Środki opóźniające palność zawierające fosfor |
| US10035896B2 (en) | 2014-07-29 | 2018-07-31 | Lanxess Solutions Us Inc. | Salts of pyrophosphonic acid as flame retardants |
| US9758640B2 (en) | 2015-01-09 | 2017-09-12 | Lanxess Solutions Us Inc. | Process stabilization of polymer compositions comprising phosphorous containing flame retardants |
| US9752009B2 (en) | 2015-01-26 | 2017-09-05 | Lanxess Solutions Us Inc. | Flame retardant polymer compositions comprising heat treated phosphorus compounds and melam |
| US9534108B2 (en) | 2015-03-13 | 2017-01-03 | Chemtura Corporation | Flame retardant epoxy resins comprising phosphorus containing flame retardants |
| DE102016213281A1 (de) * | 2016-07-20 | 2018-01-25 | Clariant Plastics & Coatings Ltd | Flammschutzmittelmischungen, ihre Herstellung und ihre Verwendung |
-
2019
- 2019-12-18 US US17/415,883 patent/US20220081536A1/en active Pending
- 2019-12-18 WO PCT/US2019/067221 patent/WO2020132095A1/en unknown
- 2019-12-18 BR BR112021011696-6A patent/BR112021011696A2/pt unknown
- 2019-12-18 KR KR1020217018527A patent/KR20210106998A/ko not_active Application Discontinuation
- 2019-12-18 SG SG11202105076YA patent/SG11202105076YA/en unknown
- 2019-12-18 JP JP2021536002A patent/JP2022515185A/ja active Pending
- 2019-12-18 CA CA3121921A patent/CA3121921A1/en active Pending
- 2019-12-18 AU AU2019403247A patent/AU2019403247A1/en active Pending
- 2019-12-18 MX MX2021007135A patent/MX2021007135A/es unknown
- 2019-12-18 CN CN201980081134.1A patent/CN113166181A/zh active Pending
- 2019-12-18 EP EP19842924.3A patent/EP3898640A1/en active Pending
-
2021
- 2021-05-19 ZA ZA2021/03393A patent/ZA202103393B/en unknown
- 2021-06-15 IL IL284017A patent/IL284017A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN113166181A (zh) | 2021-07-23 |
| US20220081536A1 (en) | 2022-03-17 |
| MX2021007135A (es) | 2021-08-11 |
| SG11202105076YA (en) | 2021-07-29 |
| AU2019403247A1 (en) | 2021-06-10 |
| EP3898640A1 (en) | 2021-10-27 |
| WO2020132095A1 (en) | 2020-06-25 |
| JP2022515185A (ja) | 2022-02-17 |
| CA3121921A1 (en) | 2020-06-25 |
| IL284017A (en) | 2021-08-31 |
| BR112021011696A2 (pt) | 2021-09-08 |
| AU2019403247A8 (en) | 2021-08-05 |
| ZA202103393B (en) | 2022-08-31 |
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